Faculty of Science and Technology, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka, 437-8555, Japan.
Faculty of Life Science and Biotechnology, Fukuyama University, 1 Gakuen-cho, Fukuyama, Hiroshima, 729-0292, Japan.
Chem Biodivers. 2023 Aug;20(8):e202300888. doi: 10.1002/cbdv.202300888. Epub 2023 Jul 31.
The marine red algal genus Laurencia has abundant halogenated secondary metabolites, which exhibit novel structural types and possess various unique biological potentials, including antifouling activity. In this study, we report the isolation, structure elucidation, and antifouling activities of two novel brominated diterpenoids, aplysin-20 aldehyde (1), 13-dehydroxyisoaplysin-20 (2), and its congeners. We screened marine red alga Laurencia venusta Yamada for their antifouling activity against the mussel Mytilus galloprovincialis. Ethyl acetate extracts of L. venusta from Hiroshima and Chiba, Japan, were isolated and purified, and the compound structures were identified using 1D and 2D NMR, HR-APCI-MS, IR, and chemical synthesis. Seven secondary metabolites were identified, and their antifouling activities were evaluated. Compounds 1, 2, and aplysin-20 (3) exhibited strong activities against M. galloprovincialis. Therefore, these compounds can be explored as natural antifouling drugs.
海洋红藻属Laurencia 富含卤代次生代谢产物，具有新颖的结构类型和各种独特的生物潜力，包括抗污活性。在这项研究中，我们报告了两种新型溴代二萜的分离、结构阐明和抗污活性，即aplysin-20 醛（1）、13-去羟基异aplysin-20（2）及其同系物。我们筛选了海洋红藻Laurencia venusta Yamada 对贻贝Mytilus galloprovincialis 的抗污活性。来自日本广岛和千叶的 L. venusta 的乙酸乙酯提取物被分离和纯化，化合物结构通过 1D 和 2D NMR、HR-APCI-MS、IR 和化学合成进行鉴定。鉴定了七种次生代谢产物，并评估了它们的抗污活性。化合物 1、2 和 aplysin-20（3）对 M. galloprovincialis 表现出强烈的活性。因此，这些化合物可以作为天然抗污药物进行探索。
